DE3038401A1 - Oxayohimban-carbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Oxayohimban-carbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE3038401A1 DE3038401A1 DE19803038401 DE3038401A DE3038401A1 DE 3038401 A1 DE3038401 A1 DE 3038401A1 DE 19803038401 DE19803038401 DE 19803038401 DE 3038401 A DE3038401 A DE 3038401A DE 3038401 A1 DE3038401 A1 DE 3038401A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- general formula
- hydrogen atom
- compounds
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 7
- -1 OXAYOHIMBAN CARBONIC ACID DERIVATIVES Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- GRTOGORTSDXSFK-UHFFFAOYSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 238000010640 amide synthesis reaction Methods 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- PEYPCTZOXFDFFW-UHFFFAOYSA-N 3-Iso-19-epi-ajnalicin Natural products C1=CC=C2C3CCN4CC5C(C)OC=C(C(=O)OC)C5CC4C3NC2=C1 PEYPCTZOXFDFFW-UHFFFAOYSA-N 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 2
- 230000007953 anoxia Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000496 anti-anoxic effect Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000003970 cerebral vascular damage Effects 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925353A FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3038401A1 true DE3038401A1 (de) | 1981-04-23 |
Family
ID=9230588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803038401 Withdrawn DE3038401A1 (de) | 1979-10-11 | 1980-10-10 | Oxayohimban-carbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5661382A (enExample) |
| AU (1) | AU6316580A (enExample) |
| BE (1) | BE885656A (enExample) |
| DE (1) | DE3038401A1 (enExample) |
| DK (1) | DK428780A (enExample) |
| ES (1) | ES8206521A1 (enExample) |
| FR (1) | FR2467206A1 (enExample) |
| GB (1) | GB2060639A (enExample) |
| GR (1) | GR70751B (enExample) |
| IL (1) | IL61246A0 (enExample) |
| IT (1) | IT1195761B (enExample) |
| LU (1) | LU82833A1 (enExample) |
| NL (1) | NL8005609A (enExample) |
| NO (1) | NO803038L (enExample) |
| PT (1) | PT71901B (enExample) |
| SE (1) | SE8007121L (enExample) |
| ZA (1) | ZA806246B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4125137A1 (de) * | 1991-07-30 | 1993-02-04 | Mauser Werke Oberndorf | Steuerpult fuer bearbeitungs- und messmaschinen |
-
1979
- 1979-10-11 FR FR7925353A patent/FR2467206A1/fr active Granted
-
1980
- 1980-10-09 ZA ZA00806246A patent/ZA806246B/xx unknown
- 1980-10-09 IT IT25251/80A patent/IT1195761B/it active
- 1980-10-09 JP JP14184380A patent/JPS5661382A/ja active Pending
- 1980-10-10 NO NO803038A patent/NO803038L/no unknown
- 1980-10-10 GB GB8032835A patent/GB2060639A/en not_active Withdrawn
- 1980-10-10 BE BE0/202429A patent/BE885656A/fr unknown
- 1980-10-10 DK DK428780A patent/DK428780A/da unknown
- 1980-10-10 ES ES495797A patent/ES8206521A1/es not_active Expired
- 1980-10-10 NL NL8005609A patent/NL8005609A/nl not_active Application Discontinuation
- 1980-10-10 AU AU63165/80A patent/AU6316580A/en not_active Abandoned
- 1980-10-10 PT PT71901A patent/PT71901B/pt unknown
- 1980-10-10 IL IL61246A patent/IL61246A0/xx unknown
- 1980-10-10 LU LU82833A patent/LU82833A1/fr unknown
- 1980-10-10 GR GR63108A patent/GR70751B/el unknown
- 1980-10-10 DE DE19803038401 patent/DE3038401A1/de not_active Withdrawn
- 1980-10-10 SE SE8007121A patent/SE8007121L/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4125137A1 (de) * | 1991-07-30 | 1993-02-04 | Mauser Werke Oberndorf | Steuerpult fuer bearbeitungs- und messmaschinen |
Also Published As
| Publication number | Publication date |
|---|---|
| IL61246A0 (en) | 1980-12-31 |
| FR2467206B1 (enExample) | 1983-01-28 |
| SE8007121L (sv) | 1981-04-12 |
| NO803038L (no) | 1981-04-13 |
| IT1195761B (it) | 1988-10-27 |
| ES495797A0 (es) | 1982-01-16 |
| ES8206521A1 (es) | 1982-01-16 |
| LU82833A1 (fr) | 1982-05-10 |
| GB2060639A (en) | 1981-05-07 |
| JPS5661382A (en) | 1981-05-26 |
| ZA806246B (en) | 1981-10-28 |
| IT8025251A0 (it) | 1980-10-09 |
| BE885656A (fr) | 1981-04-10 |
| GR70751B (enExample) | 1983-03-14 |
| PT71901B (fr) | 1981-08-31 |
| NL8005609A (nl) | 1981-04-14 |
| DK428780A (da) | 1981-04-12 |
| PT71901A (fr) | 1980-11-01 |
| AU6316580A (en) | 1981-04-16 |
| FR2467206A1 (fr) | 1981-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |